1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-(difluoromethoxy)phenyl]vinyl}-N-(4-isopropyl-1,3-thiazol-2-yl)imidazo[2,1-b][1,3]thiazole-5-carboxamide

HRID 1882160Notes

Reaction equation

HRID 1882160 reaction equation
[F:1][CH:2]([F:29])[O:3][C:4]1[C:5]([O:23][CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:6](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]3[N:18]([C:19]=2[C:20](O)=[O:21])[CH:17]=[CH:16][S:15]3)[CH:7]=[CH:8][CH:9]=1.[CH:30]([C:33]1[N:34]=[C:35]([NH2:38])[S:36][CH:37]=1)([CH3:32])[CH3:31].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C1COCC1.CN(C=O)C>[CH3:27][C:25]([CH3:28])([CH3:26])[CH2:24][O:23][C:5]1[C:4]([O:3][CH:2]([F:29])[F:1])=[CH:9][CH:8]=[CH:7][C:6]=1/[CH:10]=[CH:11]/[C:12]1[N:13]=[C:14]2[N:18]([C:19]=1[C:20]([NH:38][C:35]1[S:36][CH:37]=[C:33]([CH:30]([CH3:32])[CH3:31])[N:34]=1)=[O:21])[CH:17]=[CH:16][S:15]2

Participants

7

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70640774-(Propan-2-yl)-1,3-thiazol-2-amineHCID 684073456-{(E)-2-[3-(Difluoromethoxy)-2-(2,2-dimethylpropoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

Product 1

HCID 468332546-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-(difluoromethoxy)phenyl]vinyl}-N-(4-isopropyl-1,3-thiazol-2-yl)imidazo[2,1-b][1,3]thiazole-5-carboxamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the general procedure (Method B) by coupling Intermediate 7A (100 mg, 0.236 mmol) with 4-(isopropyl)-1,3-thiazol-2-amine (41 mg, 0.260 mmol) in the presence of EDCI hydrochloride (90 mg, 0.472 mmol) and DMAP (26 mg, 0.236 mmol) in a mixture of THF and DMF (1:1, 4 mL) to give 60 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.07 (s, 9H), 1.26 (d, J=6.9 Hz, 6H), 2.92-2.98 (m, 1H), 3.57 (s, 2H), 6.64 (s, 1H), 7.18 (t, J=74.7 Hz, 1H), 7.20-7.30 (m, 2H), 7.42 (s, 1H), 7.64-7.70 (m, 1H), 7.83 (d, J=15.6 Hz, 1H), 8.12-8.18 (m, 1H), 8.60-8.70 (m, 1H), 12.86 (br s, 1H); APCI-MS (m/z) 547.26 (MH)+.

Sources & evidence

ORD record
ord-346b4b5c9f3947e1b5dd4dc068c2e5d4
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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